View source for Shogaol

{{chembox
| Name=[6]-Shogaol
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| ImageFile=6-shogaol.svg
| ImageSize=200px
| PIN=(4''E'')-1-(4-Hydroxy-3-methoxyphenyl)dec-4-en-3-one
| OtherNames={{ubl|[6]-Shogaol|(''E'')-[6]-Shogaol| Enexasogaol}}
|Section1={{Chembox Identifiers
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| CASNo= 23513-13-5
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| CASNo2= 555-66-8
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| PubChem=5281794
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| ChEMBL = 25948
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| UNII = 83DNB5FIRF
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| InChI = 1/C17H24O3/c1-3-4-5-6-7-8-15(18)11-9-14-10-12-16(19)17(13-14)20-2/h7-8,10,12-13,19H,3-6,9,11H2,1-2H3/b8-7+
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{{Infobox pepper
| heat     = Very hot (chemical)
| scoville = 160,000<ref name="SHU"/>
}}

'''Shogaols''' are [[pungent]] constituents of [[ginger]] similar in chemical structure to [[gingerol]]. The most common of the group is '''[6]-shogaol'''.  Like [[zingerone]], it is produced when ginger is dried or cooked.<ref name="harold">{{Cite book |author = Harold McGee | date = 2004 | title = On Food and Cooking: The Science and Lore of the Kitchen | edition = 2nd | location = New York | publisher = Scribner | pages = 425–426}}</ref>  Moreover, shogaol (and [[gingerol]]) are converted to other constituents when heat is applied over time, which is why ginger loses its spiciness as it is cooked.

The name ''shogaol'' is derived from the [[Japanese language|Japanese]] name for ginger (生姜、''shōga'').

Shogaol is rated 160,000 SHU on the [[Scoville scale]].<ref name="SHU">{{Cite journal|last1=Compton|first1=Richard G.|last2=Batchelor-McAuley|first2=Christopher|last3=Ngamchuea|first3=Kamonwad|last4=Chaisiwamongkhol|first4=Korbua|date=2016-10-31|title=Electrochemical detection and quantification of gingerol species in ginger (Zingiber officinale) using multiwalled carbon nanotube modified electrodes|journal=Analyst|language=en|volume=141|issue=22|pages=6321–6328|doi=10.1039/C6AN02254E|pmid=27774555|issn=1364-5528|bibcode=2016Ana...141.6321C|s2cid=40241982 |url=https://ora.ox.ac.uk/objects/uuid:b2a3c323-180f-45b7-a462-02f397ab718f}}</ref> When compared to other pungent compounds, shogaol is moderately more pungent than [[piperine]], but 100 times less than [[capsaicin]].

{| class="wikitable"
! Compound
! Scoville Heat Units<br>(SHU)
|-
| Capsaicin
| 16,000,000<ref name="Govindarajan Sathyanarayana 1991">{{cite journal | vauthors = Govindarajan, Sathyanarayana | date = 1991 | title = Capsicum — Production, Technology, Chemistry, and Quality. Part V. Impact on Physiology, Pharmacology, Nutrition, and Metabolism; Structure, Pungency, Pain, and Desensitization Sequences | journal = Critical Reviews in Food Science and Nutrition | volume = 29 | issue = 6 | pages = 435–474 | doi = 10.1080/10408399109527536 | pmid = 2039598 }}</ref>
|-
| [6]-Shogaol
| 160,000
|-
| Piperine
| 100,000
|-
| [6]-Gingerol
| 60,000
|}

==Shogaols group==
[4]-Shogaol, [8]-shogaol, [10]-shogaol, and [12]-shogaol (all found in ginger) together constitute the group '''shogaols'''.  There also exist in ginger cultivars methylated shogaols: methyl [6]-shogaol and methyl [8]-shogaol, respectively.<ref>{{cite journal|url=http://www.hindawi.com/journals/bmri/2015/671058/tab1/|title=Analysis of Chemical Properties of Edible and Medicinal Ginger by Metabolomics Approach : Table 1|date=2015 |doi=10.1155/2015/671058 |pmid=26495311 |access-date=3 December 2016 |last1=Tanaka |first1=K. |last2=Arita |first2=M. |last3=Sakurai |first3=H. |last4=Ono |first4=N. |last5=Tezuka |first5=Y. |journal=BioMed Research International |doi-access=free |pmc=4606115 }}</ref>

Shogaols are artifacts formed during storage or through excess heat, probably created by a [[dehydration reaction]] of the gingerols. The ratio of shogaols to gingerols sometimes is taken as an indication of product quality.<ref name="nsf">[[NSF International]] ''Determination of Gingerols and Shogaols in Zingiber officinale rhizome and powdered extract by High-Performance Liquid Chromatography'' {{full citation needed|date=February 2015}}</ref>

{{Multiple image | align = left | image1 = 8-shogaol.svg | caption1 = [8]-shogaol | image2 = 10-shogaol.svg | caption2 = [10]-shogaol | total_width = 600}}{{clear-left}}

== Synthesis ==
A possible synthesis starts with a [[Claisen condensation]] of [[vanillin]] and [[acetone]], producing dehydrozingerone. Afterwards the product reacts in an [[aldol condensation]] with [[hexanal]] in [[tetrahydrofurane]] to 6-dehydroshogaol and 6-dehydrogingerol. Latter can be [[Hydrogenation|hydrogenated]] to [6]-gingerol by a catalyst. In the last step [[hydrochloric acid]] is added to get the desired [6]-shogaol.<ref>{{Cite journal|author=Hung-Cheng Shih |display-authors=etal |title=Synthesis of Analogues of Gingerol and Shogaol, the Active Pungent Principles from the Rhizomes of Zingiber officinale and Evaluation of Their Anti-Platelet Aggregation Effects.|journal=[[International Journal of Molecular Sciences]]|volume=15|number=3|date=March 2014|pages=3926–3951|pmc=3975376|pmid=24599082 |doi=10.3390/ijms15033926 |doi-access=free }}</ref>
[[File:Wikipedia-shogaol.svg|frame|center|Possible synthesis of [6]-shogaol starting from vanillin]]

==References==
{{Reflist|2}}

{{Ginger Plant}}
{{Transient receptor potential channel modulators}}

[[Category:Pungent flavors]]
[[Category:O-methylated natural phenols]]
[[Category:Ginger]]